Issue 37, 2012
From the journal:

Organic & Biomolecular Chemistry

Direct allenol-based stereocontrolled access to substituted (E)-1,3-enynes†

Benito Alcaide,*a   Pedro Almendros*b  and  Teresa Martínez del Campoa  

* Corresponding authors

a Grupo de Lactamas y Heterociclos Bioactivos, Departamento de Química Orgánica I, Unidad Asociada al CSIC, Facultad de Química, Universidad Complutense de Madrid, 28040-Madrid, Spain
E-mail: alcaideb@quim.ucm.es
Fax: +34-91-3944103

b Instituto de Química Orgánica General, IQOG, Consejo Superior de Investigaciones Científicas (CSIC), Juan de la Cierva 3, 28006-Madrid, Spain
E-mail: Palmendros@iqog.csic.es
Fax: +34-91-5644853

Abstract

A stereoselective synthesis of 1-substituted (E)-2-aryl-but-1-en-3-ynes, including tetrasubstituted alkenes, has been developed from aryl-substituted α-allenols by treatment with the AcCl–NaOH (aqueous) system. This transformation might be explained through the elimination of acetic acid, made up of a δ-hydrogen and the acetate group in the initially formed α-allenic acetate.

Graphical abstract: Direct allenol-based stereocontrolled access to substituted (E)-1,3-enynes

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Article information

DOI
https://doi.org/10.1039/C2OB26085A
Article type
Paper
Submitted
05 Jun 2012
Accepted
03 Aug 2012
First published
03 Aug 2012

Org. Biomol. Chem., 2012,10, 7603-7609

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Direct allenol-based stereocontrolled access to substituted (E)-1,3-enynes

B. Alcaide, P. Almendros and T. Martínez del Campo, Org. Biomol. Chem., 2012, 10, 7603 DOI: 10.1039/C2OB26085A

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